Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H24O |
Molecular Weight | 220.3505 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
InChI
InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N
InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
Molecular Formula | C15H24O |
Molecular Weight | 220.3505 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. BHT is a substituted derivative of phenol. BHT helps to prevent the formation of free radicals and oxidation. When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. It may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). BHT was first used as an antioxidant food additive in 1954. BHT does have other commercial uses, as in animal feeds and in the manufacture of synthetic rubber and plastics, where it also acts as an antioxidant. The U.S. Food and Drug Administration has deemed that BHT is safe enough when used in limited concentrations. It currently permits its use in concentrations of about 0.01% to 0.02% in most foods. As an emulsion stabilizer in shortening, it may be used in a somewhat higher concentration, 200 parts per million.
CNS Activity
Sources: http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=1071&AspxAutoDetectCookieSupport=1
Curator's Comment: It may cross the blood brain barrier, causing psychotropic symptoms
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19231207 |
630.0 nM [Ki] | ||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Inactive ingredient | A-TEAM Approved UseUSE HELPS PROTECT AGAINST SUNBURN Launch Date2014 |
PubMed
Title | Date | PubMed |
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Haemorrhages due to defective blood coagulation do not occur in mice and guinea-pigs fed butylated hydroxytoluene, but nephrotoxicity is found in mice. | 1992 Feb |
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Practical synthesis of chiral emopamil left hand as a bioactive motif. | 2002 Aug 23 |
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Ammonia-induced heme oxygenase-1 expression in cultured rat astrocytes and rat brain in vivo. | 2002 Dec |
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[Determination of 2,6-di-tertbutyl-4-methylphenol in an aviation jet fuel by high performance liquid chromatography]. | 2002 Jul |
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Hydrogen bonding between phenols and fatty acid esters: (1)H NMR study and ab initio calculations. | 2002 Jul 11 |
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Molecular profiling of genes up-regulated during promotion by phenobarbital treatment in a medium-term rat liver bioassay. | 2002 Jun |
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Analysis of the antioxidant butylated hydroxytoluene (BHT) in water by means of solid phase extraction combined with GC/MS. | 2002 May |
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A convenient method for determination of the C20-22 PUFA composition of glycerolipids in blood and breast milk. | 2002 May |
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Celecoxib reduces pulmonary inflammation but not lung tumorigenesis in mice. | 2002 Oct |
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Screening chemical composition and in vitro antioxidant and antimicrobial activities of the essential oils from Origanum syriacum L. growing in Turkey. | 2003 Dec |
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Antioxidizing potency of phenol compounds in olive oil mill wastewater. | 2003 Dec 17 |
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Free radical-induced protein modification and inhibition of Ca2+-ATPase of cardiac sarcoplasmic reticulum. | 2003 Jun |
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Effects of dietary butylated hydroxytoluene on aflatoxin B1-relevant metabolic enzymes in turkeys. | 2003 May |
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Trapping effect of synthetic sex pheromone of Acleris fimbriana (Lepidoptera: Tortricidae) in Chinese northern orchard. | 2003 May-Jun |
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Cytotoxicity and apoptosis induction by butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). | 2003 Nov-Dec |
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[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals]. | 2004 Apr |
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Recovery of phenolic antioxidants from wine industry by-products. | 2004 Apr |
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Structure and generation mechanism of a novel degradation product formed by oxidatively induced coupling of miconazole nitrate with butylated hydroxytoluene in a topical ointment studied by HPLC-ESI-MS and organic synthesis. | 2004 Feb |
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A critical evaluation of the factors determining the effect of intramolecular hydrogen bonding on the O-H bond dissociation enthalpy of catechol and of flavonoid antioxidants. | 2004 Feb 20 |
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Analysis of insecticidal Azadirachta indica A. Juss. fractions. | 2004 Jan-Feb |
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Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites. | 2004 Jul |
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Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress. | 2004 Jun |
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Effect of thiabendazole on some rat hepatic xenobiotic metabolising enzymes. | 2004 Jun |
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Inhibitory effects of organic acid salts on growth of Clostridium perfringens from spore inocula during chilling of marinated ground turkey breast. | 2004 Jun 1 |
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In vitro estrogenicity of resin composites. | 2004 Mar |
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[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004 May |
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Relative antioxidant capacities of propofol and its main metabolites. | 2004 Nov |
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Optimization of a high-performance liquid chromatography system by artificial neural networks for separation and determination of antioxidants. | 2004 Oct |
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Mononuclear, five-coordinate lanthanide amido and aryloxide complexes bearing tetradentate (N2O2) Schiff bases. | 2004 Oct 4 |
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Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation. | 2004 Sep 22 |
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Anticancer properties of propofol-docosahexaenoate and propofol-eicosapentaenoate on breast cancer cells. | 2005 |
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2,1,3-Benzothiadiazine derivatives: synthesis and screening versus PDE4 enzyme. | 2005 Aug |
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Synthesis, biological evaluation and molecular modelling studies on benzothiadiazine derivatives as PDE4 selective inhibitors. | 2005 Feb 15 |
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Synthesis and characterization of BHT-derived tert-butyl dendrons. | 2005 Feb 4 |
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TNF alpha potentiates glutamate neurotoxicity by inhibiting glutamate uptake in organotypic brain slice cultures: neuroprotection by NF kappa B inhibition. | 2005 Feb 9 |
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Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia. | 2005 Jan 26 |
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Single-site anionic polymerization. Monomeric ester enolaluminate propagator synthesis, molecular structure, and polymerization mechanism. | 2005 Jan 26 |
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Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry. | 2005 Oct |
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Iron-ascorbic acid-induced oxidant stress and its quenching by paraoxonase 1 in HDL and the liver: comparison between humans and rats. | 2005 Oct 1 |
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New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents. | 2006 Aug 15 |
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Polypyrroles as antioxidants: kinetic studies on reactions of bilirubin and biliverdin dimethyl esters and synthetic model compounds with peroxyl radicals in solution. Chemical calculations on selected typical structures. | 2006 Jan 6 |
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Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species. | 2006 Jul 1 |
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Attenuation of the pulmonary inflammatory response following butylated hydroxytoluene treatment of cytosolic phospholipase A2 null mice. | 2006 Jun |
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Synthesis and antioxidant activity of [60]fullerene-BHT conjugates. | 2006 Jun 2 |
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Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages. | 2006 Jun 26 |
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Cadmium-induced apoptosis in rat kidney epithelial cells involves decrease in nuclear factor-kappa B activity. | 2006 May |
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Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside. | 2006 May 31 |
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Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. | 2006 May 31 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Does immune stimulation or antioxidant therapy reduce MNU-induced placental damage via activation of Jak-STAT and NFkappaB signaling pathways? | 2007 May-Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2988845
The effect of topical therapy with 15% Butylated hydroxytoluene in mineral oil on the course of recurrent herpes simplex labialis was examined in 30 patients in a double-blind, placebo-controlled pilot study.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1900157
Curator's Comment: The effect of Butylated hydroxytoluene on the oxidation of low density lipoproteins in relation to prostacyclin synthesis was investigated in the prescence of rabbit smooth muscle cells (SMC) and Fe-containing culture medium.
Butylated hydroxytoluene (BHT) inhibited lipoprotein oxidation by IC50 values of 0.8 uM
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:08:02 GMT 2023
by
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on
Fri Dec 15 15:08:02 GMT 2023
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Record UNII |
1P9D0Z171K
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
22105
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JECFA EVALUATION |
INS-321
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CODEX ALIMENTARIUS (GSFA) |
INS-321
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NCI_THESAURUS |
C275
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CFR |
21 CFR 172.115
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34247
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m2820
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100000076384
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CHEMBL146
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6347
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D002084
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SUB11765MIG
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1082708
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C322
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1P9D0Z171K
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1P9D0Z171K
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128-37-0
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204-881-4
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DTXSID2020216
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BUTYLATED HYDROXYTOLUENE
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1848
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1147
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31404
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BUTYLATED HYDROXYTOLUENE
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PRIMARY | Description: Colourless crystals or a white or almost white, crystalline powder; odour, faint and characteristic. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS, acetone R, ether R, and arachis oil R. Category: Antioxidant. Storage: Butylated hydroxytoluene should be kept in a well-closed container, protected from light. |
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.65.pdf
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